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Identification
NameOseltamivir
Accession NumberDB00198  (APRD01148)
TypeSmall Molecule
GroupsApproved
DescriptionAn acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]
Structure
Thumb
Synonyms
(−)-oseltamivir
1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R-(3alpha,4beta,5alpha))-
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
Oseltamivir
oséltamivir
Oseltamivirum
External Identifiers
  • GS 4104
  • GS-4104
  • GS4104
  • HSDB 7433
  • RO-64-0796
  • RO-640796
  • RO64-0796
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nat-oseltamivirCapsule75 mgOralNatco Pharma (Canada) Inc2016-09-29Not applicableCanada
TamifluCapsule75 mg/1OralA S Medication Solutions1999-10-27Not applicableUs
TamifluCapsule75 mg/1OralRebel Distributors Corp1999-10-27Not applicableUs
TamifluCapsule45 mgOralRoche Registration Ltd.2002-06-20Not applicableEu
TamifluPowder, for suspension6 mg/mLOralPhysicians Total Care, Inc.2011-11-03Not applicableUs
TamifluCapsule30 mg/1OralGenentech, Inc.1999-10-27Not applicableUs
TamifluCapsule30 mgOralHoffmann La Roche Limited2008-12-01Not applicableCanada
TamifluPowder, for suspension6 mg/mLOralA S Medication Solutions2013-08-01Not applicableUs
TamifluPowder, for suspension6 mg/mLOralRebel Distributors Corp2011-07-11Not applicableUs
TamifluPowder, for suspension6 mg/mlOralRoche Registration Ltd.2002-06-20Not applicableEu
TamifluCapsule75 mgOralRoche Registration Ltd.2002-06-20Not applicableEu
TamifluPowder, for suspension6 mg/mLOralGenentech, Inc.2013-08-01Not applicableUs
TamifluCapsule75 mg/1OralDispensing Solutions, Inc.1999-10-27Not applicableUs
TamifluCapsule45 mgOralHoffmann La Roche Limited2008-12-08Not applicableCanada
TamifluCapsule75 mg/1OralA S Medication Solutions1999-10-27Not applicableUs
TamifluCapsule75 mg/1OralPhysicians Total Care, Inc.2002-10-28Not applicableUs
TamifluCapsule75 mg/1OralGenentech, Inc.1999-10-27Not applicableUs
TamifluPowder, for suspension12 mg/mlOralRoche Registration Ltd.2002-06-20Not applicableEu
TamifluPowder, for suspension12 mg/mLOralDispensing Solutions, Inc.2000-12-14Not applicableUs
TamifluCapsule75 mg/1OralREMEDYREPACK INC.2012-10-31Not applicableUs
TamifluPowder, for suspension6 mgOralHoffmann La Roche Limited2012-09-10Not applicableCanada
TamifluCapsule45 mg/1OralPhysicians Total Care, Inc.2009-10-30Not applicableUs
TamifluCapsule45 mg/1OralGenentech, Inc.1999-10-27Not applicableUs
TamifluCapsule30 mgOralRoche Registration Ltd.2002-06-20Not applicableEu
Tamiflu Capsule 75mgCapsule75 mgOralHoffmann La Roche Limited1999-12-23Not applicableCanada
Tamiflu Oral SuspensionPowder, for suspension12 mgOralHoffmann La Roche Limited2003-12-192013-12-12Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EbilfuminCapsule30 mgOralActavis Group Ptc Ehf2014-05-22Not applicableEu
EbilfuminCapsule75 mgOralActavis Group Ptc Ehf2014-05-22Not applicableEu
EbilfuminCapsule30 mgOralActavis Group Ptc Ehf2014-05-22Not applicableEu
EbilfuminCapsule75 mgOralActavis Group Ptc Ehf2014-05-22Not applicableEu
EbilfuminCapsule45 mgOralActavis Group Ptc Ehf2014-05-22Not applicableEu
EbilfuminCapsule45 mgOralActavis Group Ptc Ehf2014-05-22Not applicableEu
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AgucortNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oseltamivir phosphate
204255-11-8
Thumb
  • InChI Key: PGZUMBJQJWIWGJ-ONAKXNSWSA-N
  • Monoisotopic Mass: 410.181802964
  • Average Mass: 410.404
DBSALT000881
Categories
UNII20O93L6F9H
CAS number196618-13-0
WeightAverage: 312.4045
Monoisotopic: 312.204907394
Chemical FormulaC16H28N2O4
InChI KeyVSZGPKBBMSAYNT-RRFJBIMHSA-N
InChI
InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
IUPAC Name
ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
SMILES
CCOC(=O)C1=C[C@@H](OC(CC)CC)[[email protected]](NC(C)=O)[C@@H](N)C1
Pharmacology
IndicationOseltamivir (Tamiflu) is for the treatment of uncomplicated acute illness due to influenza infection in patients 1 year and older who have been symptomatic for no more than 2 days. It is also used for the prophylaxis of influenza in adult patients and adolescents 13 years and older.
Structured Indications
PharmacodynamicsOseltamivir is an antiviral drug, a neuraminidase inhibitor used in the treatment and prophylaxis of both influenza A and influenza B. Oseltamivir is a prodrug (usually administered as phosphate), it is hydrolysed hepatically to the active metabolite, the free carboxylate of oseltamivir (GS4071). Like zanamivir, oseltamivir acts as a transition-state analogue inhibitor of influenza neuraminidase.
Mechanism of actionOseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.
TargetKindPharmacological actionActionsOrganismUniProt ID
NeuraminidaseProteinyes
inhibitor
Influenza A virus (strain A/Chile/1/1983 H1N1)P11485 details
Liver carboxylesterase 1Proteinyes
other
HumanP23141 details
Sialidase-1Proteinunknown
inhibitor
HumanQ99519 details
Sialidase-2Proteinunknown
inhibitor
HumanQ9Y3R4 details
Related Articles
AbsorptionReadily absorbed from the gastrointestinal tract after oral administration with a bioavailability of 75%.
Volume of distribution
  • 23 to 26 L
Protein bindingOseltamivir carboxylate: low (3%), Oseltamivir free base: 42%.
Metabolism

Extensively converted to oseltamivir carboxylate by esterases located predominantly in the liver. Neither oseltamivir nor oseltamivir carboxylate is a substrate for, or inhibitor of, cytochrome P450 isoforms. At least 75% of an oral dose reaches the systemic circulation as oseltamivir carboxylate.

Route of eliminationAbsorbed oseltamivir is primarily (>90%) eliminated by conversion to oseltamivir carboxylate. Oseltamivir carboxylate is not further metabolized and is eliminated in the urine. Oseltamivir carboxylate is eliminated entirely (>99%) by renal excretion.
Half life1 to 3 hours in most subjects after oral administration.
ClearanceNot Available
ToxicityAt present, there has been no experience with overdose. Single doses of up to 1000 mg of oseltamivir have been associated with nausea and/or vomiting. Mean LD (intravenous, mouse) = 100 mg/kg.
Affected organisms
  • Influenza Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
ProbenecidThe serum concentration of the active metabolites of Oseltamivir can be increased when Oseltamivir is used in combination with Probenecid.Approved
Food Interactions
  • Take without regard to meals. Food may improve gastric tolerance.
References
Synthesis Reference

DrugSyn.org

US5763483
General References
  1. Chokephaibulkit K, Uiprasertkul M, Puthavathana P, Chearskul P, Auewarakul P, Dowell SF, Vanprapar N: A child with avian influenza A (H5N1) infection. Pediatr Infect Dis J. 2005 Feb;24(2):162-6. [PubMed:15702046 ]
  2. de Jong MD, Tran TT, Truong HK, Vo MH, Smith GJ, Nguyen VC, Bach VC, Phan TQ, Do QH, Guan Y, Peiris JS, Tran TH, Farrar J: Oseltamivir resistance during treatment of influenza A (H5N1) infection. N Engl J Med. 2005 Dec 22;353(25):2667-72. [PubMed:16371632 ]
  3. Kiso M, Mitamura K, Sakai-Tagawa Y, Shiraishi K, Kawakami C, Kimura K, Hayden FG, Sugaya N, Kawaoka Y: Resistant influenza A viruses in children treated with oseltamivir: descriptive study. Lancet. 2004 Aug 28-Sep 3;364(9436):759-65. [PubMed:15337401 ]
  4. Ward P, Small I, Smith J, Suter P, Dutkowski R: Oseltamivir (Tamiflu) and its potential for use in the event of an influenza pandemic. J Antimicrob Chemother. 2005 Feb;55 Suppl 1:i5-i21. [PubMed:15709056 ]
External Links
ATC CodesJ05AH02
AHFS Codes
  • 08:18.28
PDB EntriesNot Available
FDA labelDownload (67.2 KB)
MSDSDownload (107 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.9535
Caco-2 permeable-0.702
P-glycoprotein substrateSubstrate0.5919
P-glycoprotein inhibitor INon-inhibitor0.5415
P-glycoprotein inhibitor IINon-inhibitor0.9771
Renal organic cation transporterNon-inhibitor0.9429
CYP450 2C9 substrateNon-substrate0.9083
CYP450 2D6 substrateNon-substrate0.8276
CYP450 3A4 substrateSubstrate0.5283
CYP450 1A2 substrateNon-inhibitor0.8367
CYP450 2C9 inhibitorNon-inhibitor0.8774
CYP450 2D6 inhibitorNon-inhibitor0.9174
CYP450 2C19 inhibitorNon-inhibitor0.6677
CYP450 3A4 inhibitorNon-inhibitor0.8364
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.6907
CarcinogenicityNon-carcinogens0.8863
BiodegradationNot ready biodegradable0.6191
Rat acute toxicity2.2695 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9826
hERG inhibition (predictor II)Non-inhibitor0.9464
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral30 mg/1
CapsuleOral30 mg
CapsuleOral45 mg
CapsuleOral45 mg/1
CapsuleOral75 mg/1
Powder, for suspensionOral12 mg/mL
Powder, for suspensionOral6 mg
Powder, for suspensionOral6 mg/mL
CapsuleOral75 mg
Powder, for suspensionOral12 mg
Prices
Unit descriptionCostUnit
Tamiflu 10 30 mg capsule Box101.54USD box
Tamiflu 10 45 mg capsule Box101.54USD box
Tamiflu 10 75 mg capsule Disp Pack101.54USD disp
Tamiflu 12 mg/ml Suspension51.0USD bottle
Tamiflu 30 mg gel capsule9.76USD gel capsule
Tamiflu 45 mg gel capsule9.76USD gel capsule
Tamiflu 75 mg gel capsule9.76USD gel capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2188835 No2006-08-082016-02-26Canada
US5763483 Yes1997-02-232017-02-23Us
US5866601 Yes1996-08-022016-08-02Us
US5952375 Yes1995-08-272015-08-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.686 mg/mLALOGPS
logP1.3ALOGPS
logP1.16ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.2 m3·mol-1ChemAxon
Polarizability34.65 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Acetamide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Influenza A virus (strain A/Chile/1/1983 H1N1)
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus release. Additionally helps virus spread through the circulation by further removing sialic acids from the cell surface. These cleavages prevent self-aggregation and ensure the efficient spread of th...
Gene Name:
NA
Uniprot ID:
P11485
Molecular Weight:
51874.045 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. McKimm-Breschkin J, Trivedi T, Hampson A, Hay A, Klimov A, Tashiro M, Hayden F, Zambon M: Neuraminidase sequence analysis and susceptibilities of influenza virus clinical isolates to zanamivir and oseltamivir. Antimicrob Agents Chemother. 2003 Jul;47(7):2264-72. [PubMed:12821478 ]
  4. Du QS, Wang SQ, Chou KC: Analogue inhibitors by modifying oseltamivir based on the crystal neuraminidase structure for treating drug-resistant H5N1 virus. Biochem Biophys Res Commun. 2007 Oct 19;362(2):525-31. Epub 2007 Aug 13. [PubMed:17707775 ]
  5. Wang MZ, Tai CY, Mendel DB: Mechanism by which mutations at his274 alter sensitivity of influenza a virus n1 neuraminidase to oseltamivir carboxylate and zanamivir. Antimicrob Agents Chemother. 2002 Dec;46(12):3809-16. [PubMed:12435681 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
other
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, Yan B: Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther. 2006 Dec;319(3):1477-84. Epub 2006 Sep 11. [PubMed:16966469 ]
  2. Wattanagoon Y, Stepniewska K, Lindegardh N, Pukrittayakamee S, Silachamroon U, Piyaphanee W, Singtoroj T, Hanpithakpong W, Davies G, Tarning J, Pongtavornpinyo W, Fukuda C, Singhasivanon P, Day NP, White NJ: Pharmacokinetics of high-dose oseltamivir in healthy volunteers. Antimicrob Agents Chemother. 2009 Mar;53(3):945-52. doi: 10.1128/AAC.00588-08. Epub 2008 Dec 22. [PubMed:19104028 ]
  3. Zhu HJ, Markowitz JS: Activation of the antiviral prodrug oseltamivir is impaired by two newly identified carboxylesterase 1 variants. Drug Metab Dispos. 2009 Feb;37(2):264-7. doi: 10.1124/dmd.108.024943. Epub 2008 Nov 20. [PubMed:19022936 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Exo-alpha-sialidase activity
Specific Function:
Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage.
Gene Name:
NEU1
Uniprot ID:
Q99519
Molecular Weight:
45466.96 Da
References
  1. Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [PubMed:20222714 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Exo-alpha-(2->8)-sialidase activity
Specific Function:
Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins, oligosaccharides and gangliosides.
Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Molecular Weight:
42253.345 Da
References
  1. Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [PubMed:20222714 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Atpase activity, coupled to transmembrane movement of substances
Specific Function:
May be an organic anion pump relevant to cellular detoxification.
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular Weight:
149525.33 Da
References
  1. Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [PubMed:19029202 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Ogihara T, Kano T, Wagatsuma T, Wada S, Yabuuchi H, Enomoto S, Morimoto K, Shirasaka Y, Kobayashi S, Tamai I: Oseltamivir (tamiflu) is a substrate of peptide transporter 1. Drug Metab Dispos. 2009 Aug;37(8):1676-81. doi: 10.1124/dmd.109.026922. Epub 2009 May 13. [PubMed:19439487 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [PubMed:19029202 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 02, 2016 03:58